Phosphorus oxychloride → HCID 59443566, compound

HRID 1927680Notes

Reaction equation

HRID 1927680 reaction equation
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[CH:8]=[C:9]([C:14](=[O:38])[CH2:15][NH:16][C:17](=O)[CH2:18][CH2:19][C:20]2[N:21](S(N(C)C)(=O)=O)[CH:22]=[C:23]([CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][CH3:28])[N:24]=2)[CH:10]=[CH:11][C:12]=1[F:13].C(=O)(O)[O-].[Na+]>C(#N)C.C(Cl)Cl>[F:6][C:7]1[CH:8]=[C:9]([C:14]2[O:38][C:17]([CH2:18][CH2:19][C:20]3[NH:24][C:23]([CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][CH3:28])=[CH:22][N:21]=3)=[N:16][CH:15]=2)[CH:10]=[CH:11][C:12]=1[F:13]

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 68673301HCID 68673301, compound

Product 1

HCID 59443566HCID 59443566, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Phosphorus oxychloride (190 mg, 1.2 mmol) was added to a solution of N-[2-(3,4-difluorophenyl)-2-oxoethyl]-3-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]propanamide (for synthesis see example 234) (30 mg, 0.06 mmol) in dry acetonitrile (4 mL) at rt. After stirring at 80° C. overnight, saturated sodium bicarbonate (ca. 3 mL) was added. The aqueous phase was washed with 1:5 ethyl acetate/diethyl ether, basified with 5N aqueous sodium hydroxide and extracted with ethyl acetate. Combined extracts were washed with brine, dried (sodium sulfate) and concentrated to give a residue. The residue was dissolved in methylene chloride to give the title compound, which was acidified with 1M HCl in diethyl ether. Additional diethyl ether and hexane were added, and concentration afforded the HCl salt of the title compound. LC-MS: m/e 360 (M+H).

Workup

  1. washThe aqueous phase was washed with 1:5 ethyl acetate/diethyl ether
  2. extractionextracted with ethyl acetate
  3. washCombined extracts were washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customto give a residue

Sources & evidence

ORD record
ord-0100e74648434bda834233dac8a67087
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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